Water → HCID 10946371, compound

HRID 1647954Notes

Reaction equation

HRID 1647954 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2([C:10]3([F:13])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]([C:10]2([F:13])[CH2:12][CH2:11]2)([OH:8])[CH2:9][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 22400786HCID 22400786, compound

Product 1

HCID 10946371HCID 10946371, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.3 g (15.7 mmol) of 2-(4-chlorobenzyl)-2-(1-fluorocyclopropyl)-oxirane in 10 ml of dimethylformamide is added dropwise to a mixture of 3.3 g (47.1 mmol) of 1,2,4-triazole end 0.35 g (3.14 mmol) of potassium tert.-butylate in 20 ml of dimethylformamide at a temperature of 80° C., while stirring. When the addition has ended, the reaction mixture is stirred for 13 hours at 80° C. The solvent is then stripped off under reduced pressure, and the remaining residue is taken up with water. The aqueous phase is extracted four times with methylene chloride. The combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. The remaining residue is chromatographed over silica over silica gel using cyclohxane:ethylacetate=2:1 as the mobile phase. Evaporation of the eluate gives 2.2 g (47% of theory) of 1-(4-chlorophenyl)-2-(1-fluorocyclopropyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol in form of a solid substance.

Workup

  1. additionWhen the addition
  2. stirringthe reaction mixture is stirred for 13 hours at 80° C
  3. extractionThe aqueous phase is extracted four times with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe remaining residue is chromatographed over silica over silica gel using cyclohxane
  7. customEvaporation of the eluate

Sources & evidence

ORD record
ord-0994ba4deb4d4d23be0683ee22413642
Source dataset
uspto-grants-1995_07
Patent number
US05434303

Reaction notes

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